16749-44-3

Upstream product

• 82529-84-8 Benzoic acid 2-[(3aR,5S,6S,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 13964-22-2 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 82529-84-8 Benzoic acid (R)-2-[(3aR,5S,6S,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester 
• 3254-32-8 6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 14795-17-6 O³,O⁵-diacetyl-O⁶-benzoyl-O¹,O²-isopropylidene-β-L-idofuranose 
• 2592-45-2 O³-acetyl-O⁶-benzoyl-O¹,O²-isopropylidene-O⁵-(toluene-4-sulfonyl)-α-D-glucofuranose 
• 55263-77-9 O³,O⁶-dibenzoyl-O¹,O²-isopropylidene-O⁵-(toluene-4-sulfonyl)-α-D-glucofuranose 
• 7057-09-2 1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose 
• 19949-49-6 6-amino-O¹,O²-isopropylidene-6-deoxy-β-L-idofuranose; toluene-4-sulfonate 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 70337-36-9 Benzoic acid (2R,3S,4S,5R)-6,6-bis-benzylsulfanyl-3,4,5-trihydroxy-2-(toluene-4-sulfonyloxy)-hexyl ester 
• 51785-67-2 3,6-di-O-benzoyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-hexofuranose 
• 124572-55-0 (1R)-O²-acetyl-O³,O⁶-dibenzoyl-1-(6-benzoylamino-purin-9-yl)-D-xylo-1,4-anhydro-5-deoxy-hexitol 

Relevant academic research and scientific papers

ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL)AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS

The 4-methoxybenzyl (MPM) protecting group for hydroxy functions is readily removed with DDQ in dichloromethane containing a small amount of water at room temperature.Under these neutral conditions, several other protecting and functional groups remained unchanged. 3,4-Dimethoxybenzyl (DMPM groups are more reactive than MPM groups with DDQ.The benzyl (Bn) protecting group was removed by catalitic hydrogenation over Raney nickel.Selective deprotection of DMPM, MPM and Bn groups is also presented.

SPECIFIC REMOVAL OF O-METHOXYBENZYL PROTECTION BY DDQ OXIDATION

Methoxybenzyl protecting groups of alcohols were readily and efficiently removed with DDQ in CH2Cl2-H2O at room temperature.Under these neutral conditions, other usual protecting groups, isopropylidene, methoxymethyl, benzyloxymethyl, tetrahydropyranyl, acetyl, t-butyldimethylsilyl, benzyl, benzoyl, and tosyl, as well as functional groups, epoxide, double bond, and ketone, were remained unchanged.